A marina with modern buildings, calm water, and a clear blue sky.

Simcoe County Vacation Rentals

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Top Cities in Simcoe County

A scenic view of a hilly landscape with a dirt path leading to a viewpoint overlooking a coastal town and the ocean.
Vacation RentalsVacation Rentals

Collingwood

Collingwood

Our top choices for Simcoe County vacation rentals

A modern living room with a TV, a round coffee table, a sofa, and a view of a cityscape through large windows.

1. Stunning 1BR w Pool ~ Free Parking & Self Check-In

Stunning 1BR w Pool ~ Free Parking & Self Check-In
Innisfil
10.0 out of 10, Exceptional, (5 reviews)
"Although our stay was short, we had a wonderful experience. The host was excellent at communicating and made everything easy and seamless. The place was very clean, comfortable, and easily accessible. We really enjoyed our stay and would definitely love to come back!"
Canada
lisa
The price is CA $185
CA $334 total
includes taxes & fees
Nov 16 - Nov 17
Stunning 1BR w Pool ~ Free Parking & Self Check-In
A modern living room with a fireplace, comfortable seating, and artwork on the walls.

2. Downtown Collingwood Condos

Downtown Collingwood Condos
3.0 star property
Collingwood
9.0 out of 10, Wonderful, (48 reviews)
"Amazing place to stay. The host was awesome"
Canada
Ian
The price is CA $134
CA $310 total
includes taxes & fees
Nov 17 - Nov 18
Downtown Collingwood Condos
A lakeside view with three lounge chairs, a small table, and a stone wall.

3. Lake View Loft Studio type

Lake View Loft Studio type
Severn
8.6 out of 10, Excellent, (10 reviews)
"Beautiful please to stay and great host and will rent again for sure"
Canada
Kristopher
The price is CA $177
CA $313 total
includes taxes & fees
Nov 15 - Nov 16
Lake View Loft Studio type
A cozy living room with a brown sofa, a coffee table, and a TV. There's a kitchen area with a fridge and a sink in the background.

4. Crazy Farm C-Can Chalet

Crazy Farm C-Can Chalet
Innisfil
8.8 out of 10, Excellent, (6 reviews)
"Hospitality was on key. Enjoyed our stay"
Canada
Hannah
The price is CA $110
CA $145 total
includes taxes & fees
Dec 15 - Dec 16
Crazy Farm C-Can Chalet
An aerial view of a resort with multiple swimming pools, outdoor seating areas, and a large building with a distinctive roof.

5. Lux Studio in Horseshoe Valley

Lux Studio in Horseshoe Valley
Oro
8.8 out of 10, Excellent, (5 reviews)
"Quiet location Pool was close by Community bbq Trails nearby Nice little apartment"
Canada
Sam
The price is CA $108
CA $223 total
includes taxes & fees
Nov 15 - Nov 16
Lux Studio in Horseshoe Valley
A large, two-story house with a stone foundation and a symmetrical facade, featuring a central entrance with a red door and a covered porch.

6. Wildwood Hot Tub + Indoor/Outdoor Pool + Sauna + Game Room

Wildwood Hot Tub + Indoor/Outdoor Pool + Sauna + Game Room
Oro Medonte
9.8 out of 10, Exceptional, (11 reviews)
"Fantastic stay. We had great service from the host and enjoyed the design. It's easy to see that a lot of effort was put into the decor. We felt very at home and would definitely stay there again."
Canada
Travis
The price is CA $133
CA $344 total
includes taxes & fees
Dec 8 - Dec 9
Wildwood Hot Tub + Indoor/Outdoor Pool + Sauna + Game Room
A rooftop terrace with a fire pit, hanging chairs, and a view of modern buildings.

7. Upscale Spa Getaway w/ Private Sauna

Upscale Spa Getaway w/ Private Sauna
Innisfil
The price is CA $179
CA $368 total
includes taxes & fees
Nov 15 - Nov 16
Upscale Spa Getaway w/ Private Sauna
Terrace/patio

8. Modern Tiny Wood Cottage #3 Camping style Cottages 5 minutes to the beach!

Modern Tiny Wood Cottage #3 Camping style Cottages 5 minutes to the beach!
Wasaga Beach
8.0 out of 10, Very good, (4 reviews)
"Clean friendly easy check in and out all around great experience should recommend"
Canada
Jenna
The price is CA $176
CA $264 total
includes taxes & fees
Nov 15 - Nov 16
Modern Tiny Wood Cottage #3 Camping style Cottages 5 minutes to the beach!
Exterior

9. Sassafras Oasis Sleeps 14 - All Season Retreat Near Barrie

Sassafras Oasis Sleeps 14 - All Season Retreat Near Barrie
2.0 star property
Springwater
The price is CA $291
CA $578 total
includes taxes & fees
Nov 21 - Nov 22
Sassafras Oasis Sleeps 14 - All Season Retreat Near Barrie
A hotel room with two beds, a large window with curtains, a ceiling fan, and a painting on the wall.

10. Spacious Resort Studio in Collingwood - 9 Min from Blue Mountain!

Spacious Resort Studio in Collingwood - 9 Min from Blue Mountain!
Collingwood
9.2 out of 10, Wonderful, (32 reviews)
"Place wqs great"
United States
miguel c.
The price is CA $156
CA $264 total
includes taxes & fees
Nov 15 - Nov 16
Spacious Resort Studio in Collingwood - 9 Min from Blue Mountain!
A storefront with a large window display, a door with a sign, and a building number.

11. 124 Hurontario Unit 4

124 Hurontario Unit 4
Collingwood
9.4 out of 10, Exceptional, (3 reviews)
"Quaint, clean, comfortable, centrally located. I'd happily stay here again."
Canada
Claude
The price is CA $122
CA $327 total
includes taxes & fees
Nov 16 - Nov 17
124 Hurontario Unit 4
A wooden deck with Adirondack chairs and a table, overlooking a pool.

12. Cozy 1-Bedroom Romantic Retreat with full Kitchen

Cozy 1-Bedroom Romantic Retreat with full Kitchen
Oro-Medonte
10.0 out of 10, Exceptional, (1 review)
"What a wonderful place to stay! The hose was so welcoming from the first communication and throughout the trip. The property was exactly as described but maybe even nicer in person than the pictures. The condo was super spacious with loads of room in the main room plus the bedroom. And the bathroom! Wow! Definitely spa-like with a seperate tub and shower. Treasure is comfortable to hang out on. Instructions inside for pool and wifi were clear. The bed was super comfy! And the black out curtains...
United States
Rayissa N.
The price is CA $75
CA $195 total
includes taxes & fees
Nov 15 - Nov 16
Cozy 1-Bedroom Romantic Retreat with full Kitchen
A marina with boats docked, a clear blue sky, and a view of buildings in the distance.

13. FRIDAY HARBOUR CHIC WATERFRONT GETAWAY

FRIDAY HARBOUR CHIC WATERFRONT GETAWAY
Innisfil
9.6 out of 10, Exceptional, (7 reviews)
"Cozy space, large washroom, kitchen, perfect location!"
Canada
Elias
The price is CA $252
CA $306 total
includes taxes & fees
Nov 15 - Nov 16
FRIDAY HARBOUR CHIC WATERFRONT GETAWAY
A spacious kitchen with wooden cabinets, a central island, and a dining area with chairs.

14. Up to 40% SALE Near-Skiing-Mount Gorgeous Cottage

Up to 40% SALE Near-Skiing-Mount Gorgeous Cottage
Victoria Harbour
8.4 out of 10, Very good, (30 reviews)
"I recently rented a cottage for my family getaway, and I couldn't be happier with our choice! The cottage was absolutely huge, providing plenty of space for everyone to relax and enjoy our time together. One of the standout features was how clean everything was, especially the linens and towels, which were fresh and impeccably maintained. It made us feel right at home from the moment we arrived. Although the outside of the house is a bit creepy due to the vines that crawls all over the front...
Canada
Ellen
The price is CA $470
CA $846 total
includes taxes & fees
Nov 16 - Nov 17
Up to 40% SALE Near-Skiing-Mount Gorgeous Cottage
A glass table with a champagne bucket and glasses on a balcony with string lights.

15. Fire & Ice Spa w/ Private Sauna!

Fire & Ice Spa w/ Private Sauna!
Innisfil
10.0 out of 10, Exceptional, (13 reviews)
"Great views in a warm, fire-lit setting—perfect spot for a night out."
Canada
Craig
The price is CA $189
CA $397 total
includes taxes & fees
Nov 15 - Nov 16
Fire & Ice Spa w/ Private Sauna!
A kitchen with white cabinets, a stainless steel stove, and a refrigerator.

16. Mount St Louis Cottage

Mount St Louis Cottage
Oro-Medonte
9.4 out of 10, Exceptional, (3 reviews)
"It was an amazing and fun stay! The home was perfect and the whole location itself was also peaceful. Definitely will book it again!"
United States
denise.
The price is CA $268
CA $440 total
includes taxes & fees
Nov 16 - Nov 17
Mount St Louis Cottage
A two-story brick house with a front porch, a garage, and a well-maintained lawn.

17. Clean & Cozy Home Near Downtown

Clean & Cozy Home Near Downtown
New Tecumseth
8.6 out of 10, Excellent, (7 reviews)
"Very cozy stay for a weekend hockey tournament."
Canada
Suzanne
The price is CA $120
CA $263 total
includes taxes & fees
Dec 7 - Dec 8
Clean & Cozy Home Near Downtown
A marina at dusk with boats docked, waterfront buildings, and a calm water surface reflecting the lights.

18. Oasis Spa w/ Private Sauna!

Oasis Spa w/ Private Sauna!
Innisfil
10.0 out of 10, Exceptional, (1 review)
"The Oasis Spa Getaway was a fantastic two night stay for my partner and I. The property was clean, modern and cozy! The unit had everything a couple needs for their stay including a sauna within the unit and a beautiful balcony. The host Michelle provided exceptional hospitality and was easy to connect with when needed. The location is great and only a short walk to the boardwalk and a quick two minute drive to the Nest golf course. The building’s pool was easy to access, quiet, and relaxing....
Canada
Matthew K.
The price is CA $170
CA $358 total
includes taxes & fees
Nov 15 - Nov 16
Oasis Spa w/ Private Sauna!
Dining

19. BEACHFRONT COTTAGE IN WASAGA BEACH - SANDPIPER BEACH RESORT - COTTAGE UNIT # 12

BEACHFRONT COTTAGE IN WASAGA BEACH - SANDPIPER BEACH RESORT - COTTAGE UNIT # 12
Wasaga Beach
9.6 out of 10, Exceptional, (43 reviews)
"It was a wonderful stay, couldnt ask for a more relaxing/beautiful spot to spend the long weekend!"
United States
Alejandro G.
The price is CA $200
CA $505 total
includes taxes & fees
Dec 2 - Dec 3
BEACHFRONT COTTAGE IN WASAGA BEACH - SANDPIPER BEACH RESORT - COTTAGE UNIT # 12
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Simcoe County Hotel Reviews

Quality Inn & Conference Centre

Quality Inn & Conference Centre

10/10 Excellent
"Great stay!"
Mary 1-night trip
Posted 16 hours ago
Quality Inn & Conference Centre

Find out more about Simcoe County

Everything you need to know about Simcoe County vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Simcoe County vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Simcoe County vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Simcoe County vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Simcoe County. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Simcoe County vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Simcoe County vacation rentals we have selected for you start as low as CA $174 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Simcoe County rentals

At Expedia, we put the best Simcoe County vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Simcoe County rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Simcoe County vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Simcoe County. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.